JPS63132890A - Ｌｌ−ｆ２８２４９のモノアシルおよびジアシル誘導体 - Google Patents
Ｌｌ−ｆ２８２４９のモノアシルおよびジアシル誘導体Info
- Publication number
- JPS63132890A JPS63132890A JP62226735A JP22673587A JPS63132890A JP S63132890 A JPS63132890 A JP S63132890A JP 62226735 A JP62226735 A JP 62226735A JP 22673587 A JP22673587 A JP 22673587A JP S63132890 A JPS63132890 A JP S63132890A
- Authority
- JP
- Japan
- Prior art keywords
- hydrogen
- methyl
- isopropyl
- methoxyacetyl
- chloroacetyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 150000001875 compounds Chemical class 0.000 claims abstract description 77
- 239000000203 mixture Substances 0.000 claims abstract description 25
- 230000000749 insecticidal effect Effects 0.000 claims abstract 3
- -1 methoxyacetyl Chemical group 0.000 claims description 43
- 241001465754 Metazoa Species 0.000 claims description 30
- 229910052739 hydrogen Inorganic materials 0.000 claims description 29
- 239000001257 hydrogen Substances 0.000 claims description 29
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 23
- 150000002431 hydrogen Chemical class 0.000 claims description 22
- 238000000034 method Methods 0.000 claims description 20
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 16
- 125000002668 chloroacetyl group Chemical group ClCC(=O)* 0.000 claims description 12
- UTQNKKSJPHTPBS-UHFFFAOYSA-N 2,2,2-trichloroethanone Chemical group ClC(Cl)(Cl)[C]=O UTQNKKSJPHTPBS-UHFFFAOYSA-N 0.000 claims description 10
- 241000238631 Hexapoda Species 0.000 claims description 10
- 239000000126 substance Substances 0.000 claims description 10
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 claims description 10
- 125000001589 carboacyl group Chemical group 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 241000244206 Nematoda Species 0.000 claims description 7
- 244000078703 ectoparasite Species 0.000 claims description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- 208000015181 infectious disease Diseases 0.000 claims description 7
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 6
- 244000079386 endoparasite Species 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- 239000002689 soil Substances 0.000 claims description 2
- 230000002401 inhibitory effect Effects 0.000 claims 1
- 239000000758 substrate Substances 0.000 claims 1
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 abstract description 8
- 239000002253 acid Substances 0.000 abstract description 8
- 230000010933 acylation Effects 0.000 abstract description 6
- 238000005917 acylation reaction Methods 0.000 abstract description 6
- 230000000895 acaricidal effect Effects 0.000 abstract description 4
- 150000001805 chlorine compounds Chemical class 0.000 abstract description 3
- 238000000855 fermentation Methods 0.000 abstract description 3
- 230000004151 fermentation Effects 0.000 abstract description 3
- 241000970253 Streptomyces cyaneogriseus Species 0.000 abstract description 2
- 230000000507 anthelmentic effect Effects 0.000 abstract description 2
- 150000008064 anhydrides Chemical class 0.000 abstract 1
- 230000001984 ectoparasiticidal effect Effects 0.000 abstract 1
- 230000001069 nematicidal effect Effects 0.000 abstract 1
- 230000003389 potentiating effect Effects 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 244000045947 parasite Species 0.000 description 11
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
- 208000030852 Parasitic disease Diseases 0.000 description 9
- 238000005481 NMR spectroscopy Methods 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- 239000000284 extract Substances 0.000 description 8
- 238000011282 treatment Methods 0.000 description 8
- 238000004949 mass spectrometry Methods 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 241000282412 Homo Species 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 241000607479 Yersinia pestis Species 0.000 description 6
- 201000010099 disease Diseases 0.000 description 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 6
- 238000009472 formulation Methods 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- 241000894007 species Species 0.000 description 6
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 5
- 241000238876 Acari Species 0.000 description 5
- 125000006239 protecting group Chemical group 0.000 description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 241001465677 Ancylostomatoidea Species 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 210000001035 gastrointestinal tract Anatomy 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- YNFMRVVYUVPIAN-AQUURSMBSA-N nemadectin Chemical compound C1[C@H](O)[C@H](C)[C@@H](C(/C)=C/C(C)C)O[C@]11O[C@H](C\C=C(C)\C[C@@H](C)\C=C\C=C/2[C@]3([C@H](C(=O)O4)C=C(C)[C@@H](O)[C@H]3OC\2)O)C[C@H]4C1 YNFMRVVYUVPIAN-AQUURSMBSA-N 0.000 description 4
- YNFMRVVYUVPIAN-UHFFFAOYSA-N nemadectin alpha Natural products C1C(O)C(C)C(C(C)=CC(C)C)OC11OC(CC=C(C)CC(C)C=CC=C2C3(C(C(=O)O4)C=C(C)C(O)C3OC2)O)CC4C1 YNFMRVVYUVPIAN-UHFFFAOYSA-N 0.000 description 4
- 230000002265 prevention Effects 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- 210000001519 tissue Anatomy 0.000 description 4
- 239000003981 vehicle Substances 0.000 description 4
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical group CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 3
- JJKWHOSQTYYFAE-UHFFFAOYSA-N 2-methoxyacetyl chloride Chemical compound COCC(Cl)=O JJKWHOSQTYYFAE-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- 241000238421 Arthropoda Species 0.000 description 3
- 241000244186 Ascaris Species 0.000 description 3
- 241000283690 Bos taurus Species 0.000 description 3
- 241000282472 Canis lupus familiaris Species 0.000 description 3
- 241000196324 Embryophyta Species 0.000 description 3
- 241000283086 Equidae Species 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 241001494479 Pecora Species 0.000 description 3
- 241000244174 Strongyloides Species 0.000 description 3
- 239000000642 acaricide Substances 0.000 description 3
- 239000003242 anti bacterial agent Substances 0.000 description 3
- 229940088710 antibiotic agent Drugs 0.000 description 3
- 239000000010 aprotic solvent Substances 0.000 description 3
- 230000037396 body weight Effects 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- 239000003085 diluting agent Substances 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- 239000002917 insecticide Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 210000000056 organ Anatomy 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 2
- 241000238657 Blattella germanica Species 0.000 description 2
- 241000253350 Capillaria Species 0.000 description 2
- 241001126268 Cooperia Species 0.000 description 2
- 241000255925 Diptera Species 0.000 description 2
- 241000282326 Felis catus Species 0.000 description 2
- 241000238814 Orthoptera Species 0.000 description 2
- 241000243795 Ostertagia Species 0.000 description 2
- 241001674048 Phthiraptera Species 0.000 description 2
- 241000283984 Rodentia Species 0.000 description 2
- 241000258242 Siphonaptera Species 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- 241000187747 Streptomyces Species 0.000 description 2
- 241000282887 Suidae Species 0.000 description 2
- 241000243774 Trichinella Species 0.000 description 2
- 241001489151 Trichuris Species 0.000 description 2
- 240000008042 Zea mays Species 0.000 description 2
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 2
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 2
- 239000000370 acceptor Substances 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
- 239000000921 anthelmintic agent Substances 0.000 description 2
- 229940124339 anthelmintic agent Drugs 0.000 description 2
- 235000013339 cereals Nutrition 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 235000005822 corn Nutrition 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 239000002552 dosage form Substances 0.000 description 2
- 239000013057 ectoparasiticide Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 235000019359 magnesium stearate Nutrition 0.000 description 2
- 244000005700 microbiome Species 0.000 description 2
- 230000001617 migratory effect Effects 0.000 description 2
- LSCYTCMNCWMCQE-UHFFFAOYSA-N n-methylpyridin-4-amine Chemical compound CNC1=CC=NC=C1 LSCYTCMNCWMCQE-UHFFFAOYSA-N 0.000 description 2
- 239000005645 nematicide Substances 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 244000144977 poultry Species 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000004237 preparative chromatography Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 229940014800 succinic anhydride Drugs 0.000 description 2
- 239000003826 tablet Substances 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical group C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- PNVPNXKRAUBJGW-UHFFFAOYSA-N (2-chloroacetyl) 2-chloroacetate Chemical compound ClCC(=O)OC(=O)CCl PNVPNXKRAUBJGW-UHFFFAOYSA-N 0.000 description 1
- PEHFQQWAINXOQG-UHFFFAOYSA-N (2-methoxyacetyl) 2-methoxyacetate Chemical compound COCC(=O)OC(=O)COC PEHFQQWAINXOQG-UHFFFAOYSA-N 0.000 description 1
- ODIGIKRIUKFKHP-UHFFFAOYSA-N (n-propan-2-yloxycarbonylanilino) acetate Chemical compound CC(C)OC(=O)N(OC(C)=O)C1=CC=CC=C1 ODIGIKRIUKFKHP-UHFFFAOYSA-N 0.000 description 1
- 241000254175 Anthonomus grandis Species 0.000 description 1
- 241001124076 Aphididae Species 0.000 description 1
- 241000204727 Ascaridia Species 0.000 description 1
- 241000760149 Aspiculuris Species 0.000 description 1
- 241000131286 Attagenus Species 0.000 description 1
- 241000238658 Blattella Species 0.000 description 1
- 241000282465 Canis Species 0.000 description 1
- 241000283707 Capra Species 0.000 description 1
- 241000893172 Chabertia Species 0.000 description 1
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 1
- 241000207199 Citrus Species 0.000 description 1
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 1
- 241000692095 Cuterebra Species 0.000 description 1
- 235000019739 Dicalciumphosphate Nutrition 0.000 description 1
- 241001147667 Dictyocaulus Species 0.000 description 1
- 241000243990 Dirofilaria Species 0.000 description 1
- 235000003550 Dracunculus Nutrition 0.000 description 1
- 241000316827 Dracunculus <angiosperm> Species 0.000 description 1
- 241001660203 Gasterophilus Species 0.000 description 1
- 241000243976 Haemonchus Species 0.000 description 1
- 241000256244 Heliothis virescens Species 0.000 description 1
- 241000920462 Heterakis Species 0.000 description 1
- 241000257176 Hypoderma <fly> Species 0.000 description 1
- 206010061217 Infestation Diseases 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 208000002720 Malnutrition Diseases 0.000 description 1
- 241001143352 Meloidogyne Species 0.000 description 1
- 241000257159 Musca domestica Species 0.000 description 1
- 229910004809 Na2 SO4 Inorganic materials 0.000 description 1
- 244000061176 Nicotiana tabacum Species 0.000 description 1
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 1
- 241000510960 Oesophagostomum Species 0.000 description 1
- 241000243981 Onchocerca Species 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- 241000904715 Oxyuris Species 0.000 description 1
- 241000244187 Parascaris Species 0.000 description 1
- 235000019483 Peanut oil Nutrition 0.000 description 1
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical compound ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 1
- 241000412169 Peria Species 0.000 description 1
- 241000305186 Persectania ewingii Species 0.000 description 1
- 206010035148 Plague Diseases 0.000 description 1
- 208000035415 Reinfection Diseases 0.000 description 1
- 235000012377 Salvia columbariae var. columbariae Nutrition 0.000 description 1
- 240000005481 Salvia hispanica Species 0.000 description 1
- 235000001498 Salvia hispanica Nutrition 0.000 description 1
- 235000019764 Soybean Meal Nutrition 0.000 description 1
- 241001468227 Streptomyces avermitilis Species 0.000 description 1
- 241000975704 Syphacia Species 0.000 description 1
- 241000254105 Tenebrio Species 0.000 description 1
- 241001454295 Tetranychidae Species 0.000 description 1
- 241001454294 Tetranychus Species 0.000 description 1
- 235000011941 Tilia x europaea Nutrition 0.000 description 1
- 241000333689 Tineola Species 0.000 description 1
- 241000254086 Tribolium <beetle> Species 0.000 description 1
- 229920001938 Vegetable gum Polymers 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 150000001266 acyl halides Chemical class 0.000 description 1
- 208000007502 anemia Diseases 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 210000004204 blood vessel Anatomy 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 235000014167 chia Nutrition 0.000 description 1
- WBLIXGSTEMXDSM-UHFFFAOYSA-N chloromethane Chemical compound Cl[CH2] WBLIXGSTEMXDSM-UHFFFAOYSA-N 0.000 description 1
- 235000020971 citrus fruits Nutrition 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 235000012343 cottonseed oil Nutrition 0.000 description 1
- 239000002385 cottonseed oil Substances 0.000 description 1
- 238000012258 culturing Methods 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- NEFBYIFKOOEVPA-UHFFFAOYSA-K dicalcium phosphate Chemical compound [Ca+2].[Ca+2].[O-]P([O-])([O-])=O NEFBYIFKOOEVPA-UHFFFAOYSA-K 0.000 description 1
- 229940038472 dicalcium phosphate Drugs 0.000 description 1
- 229910000390 dicalcium phosphate Inorganic materials 0.000 description 1
- 229940043279 diisopropylamine Drugs 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 239000007884 disintegrant Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000003651 drinking water Substances 0.000 description 1
- 235000020188 drinking water Nutrition 0.000 description 1
- 238000010410 dusting Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 230000008029 eradication Effects 0.000 description 1
- 239000006052 feed supplement Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 208000035474 group of disease Diseases 0.000 description 1
- 210000002216 heart Anatomy 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 244000000013 helminth Species 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 210000000936 intestine Anatomy 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 239000004571 lime Substances 0.000 description 1
- 244000144972 livestock Species 0.000 description 1
- 239000007937 lozenge Substances 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- 210000003563 lymphoid tissue Anatomy 0.000 description 1
- 239000003120 macrolide antibiotic agent Substances 0.000 description 1
- 230000001071 malnutrition Effects 0.000 description 1
- 235000000824 malnutrition Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000003801 milling Methods 0.000 description 1
- 235000013379 molasses Nutrition 0.000 description 1
- 208000015380 nutritional deficiency disease Diseases 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 230000003071 parasitic effect Effects 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000003223 protective agent Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000009528 severe injury Effects 0.000 description 1
- 125000004469 siloxy group Chemical group [SiH3]O* 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007892 solid unit dosage form Substances 0.000 description 1
- RNVYQYLELCKWAN-UHFFFAOYSA-N solketal Chemical compound CC1(C)OCC(CO)O1 RNVYQYLELCKWAN-UHFFFAOYSA-N 0.000 description 1
- 239000004455 soybean meal Substances 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 210000004304 subcutaneous tissue Anatomy 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 235000015099 wheat brans Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/22—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains four or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/01—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing oxygen
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N49/00—Biocides, pest repellants or attractants, or plant growth regulators, containing compounds containing the group, wherein m+n>=1, both X together may also mean —Y— or a direct carbon-to-carbon bond, and the carbon atoms marked with an asterisk are not part of any ring system other than that which may be formed by the atoms X, the carbon atoms in square brackets being part of any acyclic or cyclic structure, or the group, wherein A means a carbon atom or Y, n>=0, and not more than one of these carbon atoms being a member of the same ring system, e.g. juvenile insect hormones or mimics thereof
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K20/00—Accessory food factors for animal feeding-stuffs
- A23K20/10—Organic substances
- A23K20/195—Antibiotics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- Dentistry (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Environmental Sciences (AREA)
- Polymers & Plastics (AREA)
- Food Science & Technology (AREA)
- Molecular Biology (AREA)
- Insects & Arthropods (AREA)
- Veterinary Medicine (AREA)
- Animal Husbandry (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- General Chemical & Material Sciences (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- Tropical Medicine & Parasitology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Photoreceptors In Electrophotography (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/907,281 US5149832A (en) | 1986-09-12 | 1986-09-12 | Mono and diacyl derivatives of ll-f28249 compounds |
| US907281 | 1986-09-12 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS63132890A true JPS63132890A (ja) | 1988-06-04 |
Family
ID=25423825
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP62226735A Pending JPS63132890A (ja) | 1986-09-12 | 1987-09-11 | Ｌｌ−ｆ２８２４９のモノアシルおよびジアシル誘導体 |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US5149832A (fr) |
| EP (1) | EP0259686B1 (fr) |
| JP (1) | JPS63132890A (fr) |
| KR (1) | KR880003948A (fr) |
| AT (1) | ATE96440T1 (fr) |
| AU (1) | AU593682B2 (fr) |
| BR (1) | BR8704737A (fr) |
| CA (1) | CA1317936C (fr) |
| DE (1) | DE3787942T2 (fr) |
| DK (1) | DK475487A (fr) |
| ES (1) | ES2059333T3 (fr) |
| HU (1) | HU199145B (fr) |
| IE (1) | IE62248B1 (fr) |
| IL (1) | IL83792A (fr) |
| NZ (1) | NZ221692A (fr) |
| PT (1) | PT85673B (fr) |
| ZA (1) | ZA876834B (fr) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS63238083A (ja) * | 1987-03-16 | 1988-10-04 | メルク エンド カムパニー インコーポレーテツド | アベルメクチン誘導体 |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8721378D0 (en) * | 1987-09-11 | 1987-10-21 | Glaxo Group Ltd | Chemical process |
| EP0341974B1 (fr) * | 1988-05-10 | 1996-01-24 | American Cyanamid Company | Dérivés du type macrolide |
| AU9785698A (en) | 1997-10-02 | 1999-04-27 | Microcide Pharmaceuticals, Inc. | Fungal efflux pump inhibitors |
| FR2948261B1 (fr) * | 2009-07-22 | 2015-10-30 | Sarl Herbarom Laboratoire | Procede insecticide et/ou repulsif |
| CN104860961B (zh) * | 2015-04-10 | 2017-08-04 | 新宇药业股份有限公司 | 一种制备5‑氧（对‑硝基苯甲酰）‑尼莫克汀的方法 |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS54145699A (en) * | 1977-12-19 | 1979-11-14 | Merck & Co Inc | 133halo and 133deoxy derivative of cc076 compound |
| JPS57120589A (en) * | 1981-01-20 | 1982-07-27 | Sankyo Co Ltd | 5-methoxy and 5-lower alkanoyloxy derivative, its preparation and acaricide and parasiticide |
| JPS6110589A (ja) * | 1984-06-05 | 1986-01-18 | アメリカン・サイアナミド・カンパニー | 新規化合物、その製法およびその用途 |
| JPS61280496A (ja) * | 1985-04-30 | 1986-12-11 | アメリカン・サイアナミツド・カンパニー | 新規な抗生物質化合物及びその製法 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4201861A (en) * | 1977-10-03 | 1980-05-06 | Merck & Co., Inc. | Acyl derivatives of C-076 compounds |
| USRE32034E (en) * | 1977-12-19 | 1985-11-19 | Merck & Co., Inc. | 13-Halo and 13-deoxy derivatives of C-076 compounds |
| AT396250B (de) * | 1984-09-14 | 1993-07-26 | American Cyanamid Co | Verfahren zur herstellung von neuen antibiotisch wirkenden verbindungen |
| ES8800986A1 (es) * | 1985-07-27 | 1987-12-01 | Pfizer | Un procedimiento para la produccion de un nuevo derivado de avermectina |
| AU598204B2 (en) * | 1985-09-13 | 1990-06-21 | American Cyanamid Company | Chemical derivatives of antibiotics S541 |
-
1986
- 1986-09-12 US US06/907,281 patent/US5149832A/en not_active Expired - Fee Related
-
1987
- 1987-08-25 AT AT87112277T patent/ATE96440T1/de not_active IP Right Cessation
- 1987-08-25 DE DE87112277T patent/DE3787942T2/de not_active Expired - Fee Related
- 1987-08-25 ES ES87112277T patent/ES2059333T3/es not_active Expired - Lifetime
- 1987-08-25 EP EP87112277A patent/EP0259686B1/fr not_active Expired - Lifetime
- 1987-09-06 IL IL83792A patent/IL83792A/xx not_active IP Right Cessation
- 1987-09-07 NZ NZ221692A patent/NZ221692A/xx unknown
- 1987-09-10 CA CA000546558A patent/CA1317936C/fr not_active Expired - Fee Related
- 1987-09-10 PT PT85673A patent/PT85673B/pt not_active IP Right Cessation
- 1987-09-11 JP JP62226735A patent/JPS63132890A/ja active Pending
- 1987-09-11 ZA ZA876834A patent/ZA876834B/xx unknown
- 1987-09-11 DK DK475487A patent/DK475487A/da not_active Application Discontinuation
- 1987-09-11 BR BR8704737A patent/BR8704737A/pt not_active IP Right Cessation
- 1987-09-11 AU AU78279/87A patent/AU593682B2/en not_active Ceased
- 1987-09-11 IE IE243387A patent/IE62248B1/en not_active IP Right Cessation
- 1987-09-11 KR KR870010119A patent/KR880003948A/ko not_active Application Discontinuation
- 1987-09-11 HU HU874051A patent/HU199145B/hu not_active IP Right Cessation
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS54145699A (en) * | 1977-12-19 | 1979-11-14 | Merck & Co Inc | 133halo and 133deoxy derivative of cc076 compound |
| JPS57120589A (en) * | 1981-01-20 | 1982-07-27 | Sankyo Co Ltd | 5-methoxy and 5-lower alkanoyloxy derivative, its preparation and acaricide and parasiticide |
| JPS6110589A (ja) * | 1984-06-05 | 1986-01-18 | アメリカン・サイアナミド・カンパニー | 新規化合物、その製法およびその用途 |
| JPS61280496A (ja) * | 1985-04-30 | 1986-12-11 | アメリカン・サイアナミツド・カンパニー | 新規な抗生物質化合物及びその製法 |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS63238083A (ja) * | 1987-03-16 | 1988-10-04 | メルク エンド カムパニー インコーポレーテツド | アベルメクチン誘導体 |
| JP2669635B2 (ja) * | 1987-03-16 | 1997-10-29 | メルク エンド カムパニー インコーポレーテツド | アベルメクチン誘導体 |
Also Published As
| Publication number | Publication date |
|---|---|
| IE872433L (en) | 1988-03-12 |
| IL83792A (en) | 1993-02-21 |
| PT85673A (en) | 1987-10-01 |
| CA1317936C (fr) | 1993-05-18 |
| ES2059333T3 (es) | 1994-11-16 |
| AU593682B2 (en) | 1990-02-15 |
| AU7827987A (en) | 1988-03-17 |
| PT85673B (pt) | 1990-05-31 |
| ZA876834B (en) | 1988-03-15 |
| HUT45535A (en) | 1988-07-28 |
| KR880003948A (ko) | 1988-05-31 |
| DE3787942D1 (de) | 1993-12-02 |
| IE62248B1 (en) | 1995-01-11 |
| ATE96440T1 (de) | 1993-11-15 |
| BR8704737A (pt) | 1988-05-03 |
| EP0259686A1 (fr) | 1988-03-16 |
| NZ221692A (en) | 1990-09-26 |
| US5149832A (en) | 1992-09-22 |
| DK475487D0 (da) | 1987-09-11 |
| DK475487A (da) | 1988-03-13 |
| DE3787942T2 (de) | 1994-05-11 |
| HU199145B (en) | 1990-01-29 |
| EP0259686B1 (fr) | 1993-10-27 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JPS63119486A (ja) | Ｌｌ−ｆ２８２４９化合物の２３−オキソ（ケト）および２３−イミノ誘導体 | |
| EP0259688B1 (fr) | Dérivés delta 22 des composés LL-F28249 | |
| JPS63107987A (ja) | ２３−ケト化合物の２３−イミノ誘導体 | |
| JPS63132890A (ja) | Ｌｌ−ｆ２８２４９のモノアシルおよびジアシル誘導体 | |
| JP2583946B2 (ja) | モノ−及びジエポキシｌｌ−ｆ２８２４９化合物の２３−オキソ（ケト）及び２３−イミノ誘導体 | |
| JP2703551B2 (ja) | Ｌｌ−ｆ２８２４９化合物のモノ−及びジエポキシド誘導体 | |
| JPS63115883A (ja) | １３‐デオキシｃ‐０７６‐アグリコン化合物の１３‐デオキシ‐２３‐オキソ（ケト）および２３‐イミノ誘導体 | |
| JP2622387B2 (ja) | Ｌｌ−ｆ２８２４９の２３−デオキシ誘導体 | |
| AU604096B2 (en) | 27-halo derivatives of LL-F28249 compounds | |
| EP0280928B1 (fr) | Dérivés désoxy-23 halogéno(chloro ou bromo)-27 des composés LL-F28249 | |
| JP2583947B2 (ja) | △▲上２▼▲上２▼−ｌｌ−ｆ２８２４９化合物のモノ−及びジエポキシド誘導体 | |
| CA1300617C (fr) | Derives mono et diepoxides de composes de 23-deoxy-ll-f28249 | |
| JPS63107985A (ja) | Δ↑２↑３−ｌｌ−ｆ２８２４９化合物 |